Discussion Meeting Mechanisms Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid Clark, J. S.; Baxter, C. A.; Dossetter, A. G.; Poigny,

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Presentation transcript:

Discussion Meeting Mechanisms Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid Clark, J. S.; Baxter, C. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. January 22 nd, 2008 Université de Montréal

Retrosynthetic Analysis Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 2

Synthesis of Allylbromide Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 3

Mechanism of Allylsilane Formation (Miguel) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 4

Synthesis of Diazoketone Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 5

Oxidative Cleavage Mechanism (Sébas) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 6

Grignard Addition Mechanism (Angélique) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 7

Synthesis of Diazoketone Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 8

Oxidation Mechanism (G. Pelletier) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64,

Oxidation Mechanism Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64,

Synthesis of Second Diazoketone Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 11

Synthesis of Second Diazoketone (Vincent) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 12

Synthesis of Second Diazoketone (Vincent) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 12

Diazoketone Key Cyclization (Maude) Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. 13

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Diazoketone Key Cyclization 14

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Oxygen Insertions 15

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Oxygen Insertions (Fred) 16

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Al-Mediated Rearrangement (Louis) 17

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Al-Mediated Rearrangement 18

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Final Cyclization 19

Clark, J. S.; Baxter,. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. ASAP. Most Advanced Precursor 20